This was one thing I was lacking last Friday at the Bannockburn Mountain Bike Classic, which was held in the day's peak heat hour of 4.30pm.
The race is scheduled during a very festive part of the year, so my first mistake was to miss out on some all important sleep hours the night before.
But when I arrived, there were riders much older, younger, bigger and smaller than me, so I figured this was a good indication I would breeze through, even with watery eyes and weak legs.
Intending to do the full 35km classic ride, I decided 22km would give me a nice leisurely ride before returning to Queenstown for another night of little sleep.
It all started pretty well, until 10 minutes into the race the chain of my month-old bike decided it was a good time to play up and come right off up the first hill.
Luckily, one kind gentleman, Otago Highlander Jason Rutledge, stopped to help a lady in need and I was back on the bike within five minutes.
I had time to make up, so I powered on up the road with no real struggle until the 22km sport turn-off gave me a run for my money.
The hill climb was something I probably should have prepared myself a little more for, but I did make the top without getting off the pedals and it made me appreciate the downhill rides slightly more.
Downhill was something I had prepared myself for, and so I ripped down the hillsides, through the mud ponds and into the tussocks.
Possibly, my confidence was what got me into my next situation.
I noticed the tussocks were getting bigger and the track was getting less visible - I had gone off the track - way off.
My legs had taken a beating from the gorse and I was getting a little bit worried about where I might end up in the "outback" of Bannockburn.
Another kind stranger called out from the roadside and told me I had missed the turn-off.
I was on for another few kilometres until my chain fell off again when attempting another giant hill.
This time it was my hands that wore the grease and scrapes, as I managed to pull the chain out from its tight hold between a screw and the back-wheel cog.
Only 10m later the chain came off for its third and final time, and it was another great stranger who offered me some help.
Surely, this would be my last hiccup of the race.
The last 5km or so were the happiest for me. My chain stayed on, there were fewer mountains and, of course, I could sense the finish line.
When I got there, I threw down my bike with anger and then quickly apologised, as I knew it was my own preparation that turned my first bike "race" into a bit of a struggle.
I was not the only one who had trouble, as my older brother had become lost in the classic section and my cousin lost his bike tyre - perhaps it's just a Caldwell thing.
Overall, however, I enjoyed the ride, the scenery and the great atmosphere of the Bannockburn Classic.
Next race, Motatapu.